EP2647657A1 - Procédé de production d'un caoutchouc diénique conjugué et modifié, caoutchouc diénique conjugué et modifié et composition de caoutchouc - Google Patents

Procédé de production d'un caoutchouc diénique conjugué et modifié, caoutchouc diénique conjugué et modifié et composition de caoutchouc Download PDF

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Publication number
EP2647657A1
EP2647657A1 EP11845388.5A EP11845388A EP2647657A1 EP 2647657 A1 EP2647657 A1 EP 2647657A1 EP 11845388 A EP11845388 A EP 11845388A EP 2647657 A1 EP2647657 A1 EP 2647657A1
Authority
EP
European Patent Office
Prior art keywords
group
modified conjugated
conjugated diene
diene rubber
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP11845388.5A
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German (de)
English (en)
Other versions
EP2647657B1 (fr
EP2647657A4 (fr
Inventor
Ryouji Tanaka
Naoya Nosaka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JSR Corp
Original Assignee
JSR Corp
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Publication date
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Publication of EP2647657A4 publication Critical patent/EP2647657A4/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
    • C08C19/00—Chemical modification of rubber
    • C08C19/25—Incorporating silicon atoms into the molecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C08F36/06—Butadiene
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • B60C1/0016—Compositions of the tread
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
    • C08C19/00—Chemical modification of rubber
    • C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
    • C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
    • C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L15/00—Compositions of rubber derivatives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
    • C08L9/06—Copolymers with styrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
    • C08C19/00—Chemical modification of rubber
    • C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule

Definitions

  • conjugated diene polymer having an alkali-metal or alkaline-earth-metal active end examples include anionic polymers obtained by polymerizing a conjugated diene compound alone or copolymerizing a conjugated diene compound and an aromatic vinyl compound.
  • Examples of the compound that has a group containing sulfur in which one hydrogen atom of a thiol has been replaced by one protecting group and that further has an alkoxysilyl group include S-trimethylsilylmercaptopropylmethyldimethoxysilane, S-trimethylsilylmercaptopropyltrimethoxysilane, S-trimethylsilylmercaptopropyltriethoxysilane, S-trimethylsilylmercaptopropylmethyldiethoxysilane, S-trimethylsilylmercaptoethyltrimethoxysilane, S-trimethylsilylmercaptoethyltriethoxysilane, S-trimethylsilylmercaptoethylmethyldimethoxysilane, and S-trimethylsilylmercaptoethylmethyldiethoxysilane.
  • suitable examples thereof include polyglycidyl ethers of polyhydric alcohols, such as ethylene glycol diglycidyl ether and glycerol triglycidyl ether, polyglycidyl ethers of aromatic compounds having two or more phenyl groups, such as the diglycidyl ether of bisphenol A, 1,4-diglycidylbenzene, 1,3,5-triglycidylbenzene, and polyepoxy compounds such as polyepoxidized liquid polybutadiene, epoxy-containing tertiary amines such as 4,4'-diglycidyldiphenylmethylamine and 4,4'-diglycidyldibenzylmethylamine, glycidylamino compounds such as diglycidylaniline, diglycidyl-o-toluidine, tetraglycidyl-m-xylenediamine, tetraglycidylaminodiphenylmethan
  • the modified conjugated diene rubber of the present invention is a modified conjugated diene rubber obtained by the method of the present invention for producing a modified conjugated diene rubber explained above.
  • the modified conjugated diene rubber has a high Mooney viscosity, excellent shape stability, and satisfactory processability.
  • the Mooney viscosity (ML1+4, 100°C) of the modified conjugated diene rubber of the present invention is preferably from 30-150, more preferably from 40-120. In case where the Mooney viscosity (ML1+4, 100°C) thereof is less than 30, shape stability decreases.
  • the rubber composition of the present invention contains, as a rubber component, the modified conjugated diene rubber described above. Details thereof are explained below.
  • silica examples include wet-process silica (hydrous silicic acid), dry-process silica (silicic acid anhydride), colloidal silica, precipitated silica, calcium silicate, and aluminum silicate.
  • wet-process silica which is most superior in the effect of improving fracture resistance and in the effect of attaining both wet grip performance and low-rolling-resistance characteristics is preferable.
  • high dispersible type silica from the standpoints of properties and processability since the silica has satisfactory dispersibility in rubbers.
  • One silica can be used alone, or two or more silicas can be used in combination.
  • silica is incorporated as a reinforcement into the rubber composition of the present invention
  • a silane coupling agent in order to further improve the reinforcing effect.
  • the silane coupling agent include bis(3-triethoxysilylpropyl) tetrasulfide, bis(3-triethoxysilylpropyl) trisulfide, bis(3-triethoxysilylpropyl) disulfide, bis(2-triethoxysilylethyl) tetrasulfide, bis(3-trimethoxysilylpropyl) tetrasulfide, bis(2-trimethoxysilylethyl) tetrasulfide, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, 2-mercaptoethyltrimethoxysilane, 2-mercaptoethyltriethoxysilane, 3-
  • Various kinds of chemicals, additives, etc. which are in general use in the rubber industry can be incorporated into the rubber composition of the present invention according to need so long as the incorporation thereof does not impair the objects of the present invention.
  • examples of various chemicals, additives, etc. which can be incorporated into the rubber composition of the present invention include a crosslinking agent (e.g., vulcanizing agent), vulcanization aid, processing aid, vulcanization accelerator, process oil, antioxidant, scorch retarder, zinc white, and stearic acid.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Silicon Polymers (AREA)
EP11845388.5A 2010-12-01 2011-11-28 Procédé de production d'un caoutchouc diénique conjugué et modifié, caoutchouc diénique conjugué et modifié et composition de caoutchouc Active EP2647657B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2010268132 2010-12-01
PCT/JP2011/077357 WO2012073880A1 (fr) 2010-12-01 2011-11-28 Procédé de production d'un caoutchouc diénique conjugué et modifié, caoutchouc diénique conjugué et modifié et composition de caoutchouc

Publications (3)

Publication Number Publication Date
EP2647657A1 true EP2647657A1 (fr) 2013-10-09
EP2647657A4 EP2647657A4 (fr) 2014-09-10
EP2647657B1 EP2647657B1 (fr) 2016-03-02

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP11845388.5A Active EP2647657B1 (fr) 2010-12-01 2011-11-28 Procédé de production d'un caoutchouc diénique conjugué et modifié, caoutchouc diénique conjugué et modifié et composition de caoutchouc

Country Status (10)

Country Link
US (1) US8980987B2 (fr)
EP (1) EP2647657B1 (fr)
JP (1) JP6003651B2 (fr)
KR (1) KR101824466B1 (fr)
CN (1) CN103237833B (fr)
BR (1) BR112013013418B8 (fr)
HU (1) HUE029141T2 (fr)
SG (1) SG190443A1 (fr)
TW (1) TWI510502B (fr)
WO (1) WO2012073880A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2902415A4 (fr) * 2012-09-25 2016-05-18 Jsr Corp Procédé de fabrication de polymère de diène conjugué modifié, composition de polymère, polymère réticulé et pneumatique
EP2876115A4 (fr) * 2012-07-20 2016-05-25 Jsr Corp Procédé de production d'un polymère de diène conjugué modifié, polymère de diène conjugué modifié, composition polymère, polymère réticulé, et pneu
EP3093297A4 (fr) * 2014-11-13 2017-01-18 LG Chem, Ltd. Polymère diène conjugué modifié, procédé de préparation dudit polymère et composition de caoutchouc contenant ce polymère
KR20170042257A (ko) * 2015-10-08 2017-04-18 주식회사 엘지화학 변성 공액디엔계 중합체, 이의 제조방법 및 이를 포함하는 고무 조성물
EP3106469A4 (fr) * 2015-01-05 2017-05-03 LG Chem, Ltd. Polymère diène conjugué modifié, composition de caoutchouc modifiée le comprenant, et procédé de préparation de polymère diène conjugué modifié
US10266614B2 (en) 2015-01-05 2019-04-23 Lg Chem, Ltd. Modified conjugated diene polymer, modified rubber composition comprising same, and method for preparing modified conjugated diene polymer
EP3383949A4 (fr) * 2015-11-30 2019-10-30 Bridgestone Americas Tire Operations, LLC Composition de caoutchouc contenant un mélange de silices et procédés associés pour améliorer l'usure

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2664626B1 (fr) 2011-01-12 2016-04-06 JSR Corporation Caoutchouc diénique conjugué, procédé de production, et composition du caoutchouc
JP6047460B2 (ja) * 2013-07-31 2016-12-21 東洋ゴム工業株式会社 タイヤ用ゴム組成物及び空気入りタイヤ
DE112014003521T5 (de) * 2013-07-31 2016-04-14 Toyo Tire & Rubber Co., Ltd. Kautschuk-Siliziumoxid-Verbundwerkstoff und Verfahren zur Herstellung desselben und Kautschukzusammensetzung und pneumatischer Reifen
JP6047459B2 (ja) * 2013-07-31 2016-12-21 東洋ゴム工業株式会社 ゴム−シリカ複合体及びその製造方法
KR101656144B1 (ko) * 2013-09-30 2016-09-08 주식회사 엘지화학 개질 공액 디엔계 중합체, 그 제조방법 및 이를 포함하는 고무 조성물
KR101700012B1 (ko) * 2014-12-22 2017-01-25 한화토탈 주식회사 변성 공액디엔계 중합체 및 그를 포함하는 조성물
JP6299638B2 (ja) * 2015-03-20 2018-03-28 信越化学工業株式会社 オルガノポリフルオロシロキサンの製造方法
JPWO2017026288A1 (ja) * 2015-08-10 2018-05-31 Jsr株式会社 共役ジエン系重合体及びその製造方法、重合体組成物、架橋重合体、並びにタイヤ
TWI663177B (zh) * 2015-09-21 2019-06-21 日商Ｅｔｉｃ有限公司 二氧化矽調配用改質溶液聚合二烯系橡膠的製造方法及其橡膠組成物
PT3508526T (pt) * 2016-09-02 2023-07-19 Kuraray Co Composição de borracha
JP2020090665A (ja) * 2018-11-27 2020-06-11 Ｔｏｙｏ Ｔｉｒｅ株式会社 防振ゴム用ゴム組成物および防振ゴム
CN118507104B (zh) * 2024-07-17 2024-09-20 常州碳禾新材料科技有限公司 一种低温导电银浆及其制备方法

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CN100347208C (zh) 2001-09-27 2007-11-07 Jsr株式会社 共轭二烯均聚或共聚橡胶、均聚或共聚橡胶的制造方法、橡胶组合物、复合体以及轮胎
JP4117250B2 (ja) * 2001-11-27 2008-07-16 株式会社ブリヂストン 共役ジエン系重合体、その製法及びそれを用いたゴム組成物
US7288594B2 (en) 2001-12-03 2007-10-30 Bridgestone Corporation Process for producing modified polymer modified polymer obtained by the process and rubber composition
JP2006137858A (ja) 2004-11-12 2006-06-01 Yokohama Rubber Co Ltd:The 共役ジエン系重合体及びそれを含むゴム組成物
CN101268107B (zh) * 2005-09-22 2012-10-10 旭化成化学株式会社 共轭二烯系聚合物及其制造方法
EP2045272B1 (fr) * 2006-07-24 2010-12-29 Asahi Kasei Chemicals Corporation Polymère de diène conjugué modifié et procédé de production de celui-ci
US20080103261A1 (en) 2006-10-25 2008-05-01 Bridgestone Corporation Process for producing modified conjugated diene based polymer, modified conjugated diene based polymer produced by the process, rubber composition, and tire
KR101475966B1 (ko) * 2007-03-23 2014-12-23 제이에스알 가부시끼가이샤 변성 공액 디엔계 중합체의 제조 방법, 변성 공액 디엔계 중합체 및 고무 조성물
CN101889050A (zh) 2007-12-07 2010-11-17 株式会社普利司通 轮胎
US20110160388A1 (en) 2008-04-30 2011-06-30 Bridgestone Corporation Process for production of modified conjugated diene copolymer, modified conjugated diene copolymer produced by the process, rubber composition, and tire
US8809440B2 (en) 2009-10-21 2014-08-19 Jsr Corporation Method of producing modified conjugated diene rubber, modified conjugated diene rubber, and rubber composition

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2876115A4 (fr) * 2012-07-20 2016-05-25 Jsr Corp Procédé de production d'un polymère de diène conjugué modifié, polymère de diène conjugué modifié, composition polymère, polymère réticulé, et pneu
EP2902415A4 (fr) * 2012-09-25 2016-05-18 Jsr Corp Procédé de fabrication de polymère de diène conjugué modifié, composition de polymère, polymère réticulé et pneumatique
EP3093297A4 (fr) * 2014-11-13 2017-01-18 LG Chem, Ltd. Polymère diène conjugué modifié, procédé de préparation dudit polymère et composition de caoutchouc contenant ce polymère
US9725527B2 (en) 2014-11-13 2017-08-08 Lg Chem, Ltd. Modified conjugated diene polymer, method for preparing same, and rubber composition containing same
EP3106469A4 (fr) * 2015-01-05 2017-05-03 LG Chem, Ltd. Polymère diène conjugué modifié, composition de caoutchouc modifiée le comprenant, et procédé de préparation de polymère diène conjugué modifié
US10266614B2 (en) 2015-01-05 2019-04-23 Lg Chem, Ltd. Modified conjugated diene polymer, modified rubber composition comprising same, and method for preparing modified conjugated diene polymer
KR20170042257A (ko) * 2015-10-08 2017-04-18 주식회사 엘지화학 변성 공액디엔계 중합체, 이의 제조방법 및 이를 포함하는 고무 조성물
EP3246344A4 (fr) * 2015-10-08 2018-01-10 LG Chem, Ltd. Polymère diénique conjugué modifié, procédé de préparation associé et composition de caoutchouc le contenant
KR101889156B1 (ko) 2015-10-08 2018-09-20 주식회사 엘지화학 변성 공액디엔계 중합체, 이의 제조방법 및 이를 포함하는 고무 조성물
US10414841B2 (en) 2015-10-08 2019-09-17 Lg Chem, Ltd. Modified conjugated diene-based polymer, method for preparing the same and rubber composition including the same
EP3383949A4 (fr) * 2015-11-30 2019-10-30 Bridgestone Americas Tire Operations, LLC Composition de caoutchouc contenant un mélange de silices et procédés associés pour améliorer l'usure
US10654993B2 (en) 2015-11-30 2020-05-19 Bridgestone Americas Tire Operations, Llc Rubber composition containing a blend of silicas and related processes for improving wear

Also Published As

Publication number Publication date
JP6003651B2 (ja) 2016-10-05
SG190443A1 (en) 2013-07-31
US8980987B2 (en) 2015-03-17
KR101824466B1 (ko) 2018-02-01
HUE029141T2 (hu) 2017-02-28
CN103237833A (zh) 2013-08-07
BR112013013418B1 (pt) 2020-12-15
JPWO2012073880A1 (ja) 2014-05-19
CN103237833B (zh) 2015-08-05
BR112013013418A2 (pt) 2016-09-06
US20130245192A1 (en) 2013-09-19
EP2647657B1 (fr) 2016-03-02
WO2012073880A1 (fr) 2012-06-07
TW201233688A (en) 2012-08-16
EP2647657A4 (fr) 2014-09-10
KR20130139992A (ko) 2013-12-23
TWI510502B (zh) 2015-12-01
BR112013013418B8 (pt) 2023-04-18

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